Now, Stessa just dumped all my transactions going back two years and I have to manually import them and recategorize everything. 

You should check if the bank feeds work with your bank otherwise, it's a deal breaker unless you don't mind manually doing the data entry.

These LOCs are typically interest only and adjustable rate, which of course is planned for, again with the equity and the cash flow of the investment, it shouldnt be a problem to at the very least break even, even in the worst of scenarios.

This adjustment stabilizes income for many, and a healthier vacation rental market is anticipated by next year.

Your true return has to be risk adjusted.  

Adjusting the purchase price, budget, and offers can help you reach the break-even point.Many calculators overestimate cost assumptions or rental comps, which can be both beneficial and a hindrance.

The LOC adjusts each year.

Just go through them, select the renovated/closely matching ones, and enter them into a model.Here's my fix & flip model, you can see the comps entered and some quick stats below them: Then I use that comp data to adjust the Sale Price in the model to what I estimate it will be (double check the resale $/sf is in-line with the comps), then adjust the purchase price until I hit my desired return level. 

adjust your price, be aggressive on it and it will rent.

The key is to be ready, wait for the right property, and adjust your offer based on the strategy you want to deploy.The time of year is less important than the property itself.